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Noise Cancelling headset

Personally I have never been able to achieve a really good fit with any foam plugs (or similar device) I've tried (and that's true of the Comply tips).

Looking back I realize I should have clarified this point.

While I don't feel that anything I've tried really fits my ear cannals perfectly, especially the right side, the Comply tips still give me a significant passive noise reduction over the Bose ear pieces.

Certainly the passive noise reduction is not as effective as the active noise reduction, but on more than one occaision I have gone an hour before realizing I had not switched the Bose power on. It's enough of a benefit to get me to put up with the stuffed ear feeling.
 
Regarding ear buds, everyone's ear canal anatomy is different. Moreover, the anatomy of your left and right ear canals will also differ. So finding a well fitting ear bud/plug isn't just an individual thing, but an individual ear thing.

This is true, however, the Bose ear buds only fit inside the outer ear and don't try to block ambient noise passively by fitting inside the canal. A small microphone senses ambient sound and creates an out of phase signal of the same amplitude to actively cancel the sound entering the ear canal. This technology first appeared in David Clark aviation headsets around 35 years ago when I was still flying. Shortly after, Telex, Bose, and some others came out with competing models. Back then they were very expensive even by aviation norms and they only performed OK, but not great. Since that was a long time ago, I imagine that the technology has had ample time to mature.
 
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